Here is how I thought it works: goes to the first 'when', evals the first condition ((({1 === String}))), sees it's false and proceeds to the next (({when})) (or (({else}))) and happily returns (({:no})).

As it turns out, even if one of AND joined conditions was false, ruby would still try to eval other conditions, and as soon as it calls the block with 1, (({NoMethodError})) gets thrown as there is no (({#blah})) on Integer.

I believe this is incorrect behavior and conditions with AND in case/when should behave like everywhere else.